Benzylamine → (1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane

HRID 1089227ノート

反応式

HRID 1089227 の反応式
[C:1]1([CH3:38])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C@@H:13](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][C@@H:11]2[CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[C:1]1([CH3:38])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:14][C@H:13]3[CH2:12][C@@H:11]2[CH2:26][N:46]3[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 7504Benzylamine2 回HCID 15629272((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

生成物 1

HCID 14612539(1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane収率 90%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2697 g (4.653 moles) of (2R, 4S)-1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)pyrrolidine and 1640 g (15.304 moles) of benzylamine in 15 L of toluene was heated under reflux. Ater 6 hours 100 g of benzylamine were added and the reflux continued for 3 hours. The mixture was cooled, filtered and the residue was washed with 5 L of toluene. The combined organic layers were evaporated to dryness and the resulting solid was taken up with 2 L of isopropanol. After cooling the product was filtered, washed with cold isopropanol and dried under reduced pressure to give 1434 g of the titled compound. (90%). M.P.=124° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe residue was washed with 5 L of toluene
  6. customThe combined organic layers were evaporated to dryness
  7. temperatureAfter cooling the product
  8. filtrationwas filtered
  9. washwashed with cold isopropanol
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-634b98ba4f0b4b70b5ab016ff17a7fcc
出典データセット
uspto-grants-1990_10
特許番号
US04965273

反応ノート

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